A homeless man was sentenced Thursday to at least 50 years in prison  in attacks on three women over two days just after Christmas in 2013, according to prosecutors and court records.

James Whiteside, 33, pleaded guilty before Cook County Judge Nicholas Ford to three counts of aggravated criminal sexual assault in the three attacks, according to prosecutors and court records. The attacks took place Dec. 26 and Dec. 27, 2013, at Midway Airport and in the Montclare and Rogers Park neighborhoods.

The first attack took place in the 7000 block of North Clark Street about 10:15 a.m. Dec. 26, 2013, according to police and court records. Whiteside attacked a woman with a knife, sexually assaulted her and took her money before fleeing, police said when he was charged.

The next attack happened about 2:30 a.m. Dec. 27. Whiteside attacked a woman as she tried to get into her car outside a White Castle restaurant near Belmont and Harlem avenues, according to police. Armed with scissors, Whiteside threatened to kill the woman, then drove her to a nearby side street and sexually assaulted her, according to a police report.

Whiteside then drove the woman until the car broke down on Diversey Avenue, and forced the woman to withdraw money from an ATM. He used $50 stolen from the victim to get a stranger to drive him to his aunt’s house in West Humboldt Park, stopping at a McDonald’s along the way, according to the report.

Whiteside called a cab and took the woman and two children with him to a McDonald’s, then back to near where he first attacked her at Belmont and Harlem. The woman then called 911.

The third attack took place about 4:15 p.m. Dec. 27, beginning in a secured parking lot off the Orange Line at Midway Airport at 4600 W. 59th St. Whiteside pushed a 69-year-old woman into her car as she opened her door and demanded money from her before he sexually her, according to a police report.

Whiteside then drove her to the West Side and repeatedly threatened her, buying drugs twice, picking up a woman he knew, driving to a liquor store and taking $200 from an ATM using the victim’s card, according to the police report.

Whiteside eventually left the victim and her car in the West Garfield Park neighborhood at Madison Street and Pulaski Road.

The victim called 911 but left the area to report the crime from closer to home, according to the report.

Whiteside “implicated himself” in the attacks in conversations with other people and gave details consistent with the victim’s account, according to his arrest report in Dec. 27 attacks. He told residents he “robbed and raped a woman the night before,” according to the report.

Whiteside, who had given his address as being in the 600 block of West Deming Place when he was arrested, but who authorities said was homeless, originally had been charged in two other attacks, but charges were dropped in those cases when he pleaded guilty Thursday.

One of the attacks involved a 29-year-old woman whom he accosted in the 1200 block of North Milwaukee Avenue about 1:55 p.m. Dec. 24, 2013, and demanded her money and car keys while holding a knife. The woman’s 3-year-old daughter also was in the car during the attack, police said at the time Whiteside was charged. But when Whiteside saw the woman’s husband walking up, he fled through a parking lot, according to a police report.

Whiteside also had been charged in an armed robbery and kidnapping attack that took place about 5:10 a.m. Dec. 16, 2013, in the 5900 block of South Kilbourn Avenue, according to court and police records.

Chicago Tribune’s Deanese Williams-Harrris contributed.

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